Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A New Carboxylate Selective Anion Receptor Utilizing Amide and Carbamate Hydrogens

  • Lee, Sung-Kyu (Department of Chemistry, Institute for Chemical Biology, Sejong University) ;
  • Kang, Jong-Min (Department of Chemistry, Institute for Chemical Biology, Sejong University)
  • Received : 2011.05.09
  • Accepted : 2011.05.17
  • Published : 2011.09.20
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Abstract

A new anion receptor utilizing carbamate functionality as hydrogen bonding site has been designed and synthesized. This new receptor 2 has two amide hydrogens and two carbamate hydrogens anchored at 1,8-position of anthracene. These four hydrogens form a concave structure for the anions and the receptor 2 was found to be a selective receptor for acetate among the anions investigated.

Keywords

References

  1. Haugland, R. P. The Handbook. A Guide to Fluorescent Probes and Labeling Technologies, 10th ed.; Molecular Probes Inc.: Eugene, OR, 2005.
  2. Anion Sensing; Stibor, I., Ed.; Springer- Verlag: Berlin 2005.
  3. Lhotak, P. Top. Curr. Chem. 2005, 255, 65.
  4. Matthews, S. E.; Beer, P. D. Supramol. Chem. 2005, 17, 411. https://doi.org/10.1080/10610270500127089
  5. Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419. https://doi.org/10.1021/cr010421e
  6. Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486. https://doi.org/10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.0.CO;2-P
  7. Haryley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Parkin Trans. 1 2000. 19, 3155.
  8. de Silva, A. P.; Nimal Gunaratne, H. Q.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515. https://doi.org/10.1021/cr960386p
  9. Fluorescent Chemosensors for Ion and Molecule Recognition; Czarnik, A. W., Ed.; American Chemical Society Books: Washington, DC, 1993.
  10. Bao, X.; Zhou, Y. Sensors and Actuators B: Chem. 2010, 147, 434. https://doi.org/10.1016/j.snb.2010.03.068
  11. Chmielewski, M. J.; Jurczak, J. Chem. Eur. J. 2005, 11, 6080. https://doi.org/10.1002/chem.200500232
  12. Kondo, S.-I.; Hiraoka, Y.; Kurumatani, N.; Yano, Y. Chem. Commun. 2005, 1720.
  13. Xie, H.; Yi, S.; Wu, S. J. Chem. Soc., Perkin Trans. 2 1999, 2751.
  14. Sessler, J. L.; An, D.; Cho, W.-S.; Lynch, V.; Marquez, M. Chem. Eur. J. 2005, 11, 2001. https://doi.org/10.1002/chem.200400894
  15. Chellappan, K.; Singh, N. J.; Hwang, I.-C.; Lee, J. W.; Kim, K. S. Angew. Chem. Int. Ed. 2005, 44, 2899. https://doi.org/10.1002/anie.200500119
  16. Nishiyabu, R.; Anzenbacher, P., Jr. J. Am. Chem. Soc. 2005, 127, 8270. https://doi.org/10.1021/ja051421p
  17. Kang, S. O.; Linares, J. M.; Powell, D.; VanderVelde, D.; Bowman- James, K. J. Am Chem. Soc. 2003, 125, 10152. https://doi.org/10.1021/ja034969+
  18. Boiocchi, M.; Boca, L. D.; Gomez, D. E.; Fabbrizzi, L.; Licchelli, M.; Monzani, E. J. Am. Chem. Soc. 2004, 126, 16507. https://doi.org/10.1021/ja045936c
  19. Kwon, J. Y.; Jang, Y. J.; Kim, S. K.; Lee, K. H.; Kim, J. S.; Yoon, J. Y. J. Org. Chem. 2004, 69, 5155. https://doi.org/10.1021/jo049281+
  20. Ayling, A. J.; Perez- Payan, M. N.; Davis, A. P. J. Am. Chem. Soc. 2001, 123, 12716. https://doi.org/10.1021/ja016796z
  21. Werner, F.; Schneider, H.-J. Helv. Chim. Acta 2000, 83, 465. https://doi.org/10.1002/(SICI)1522-2675(20000216)83:2<465::AID-HLCA465>3.0.CO;2-F
  22. Snellink-Ruel, B. H. M.; Antonisse, M. M. G.; Engbersen, J. F. J.; Timmerman, P.; Reinhoudt, D. N. Eur. J. Org. Chem. 2000, 165.
  23. Pfeffer, F. M.; Gunnlaugsson, T.; Jensen, P.; Kruger, P. E. Org. Lett. 2005, 7, 5357. https://doi.org/10.1021/ol051497q
  24. Liu, S. Y.; Fang, L.; He, Y. B.; Chan, W. H.; Yeung, K. T.; Cheng, Y. K.; Yang, R. H. Org. Lett. 2005, 7, 5825. https://doi.org/10.1021/ol052341t
  25. Gunnlaugsson, T.; Davis, A. P.; O'Brien, J. E.; Glynn, M. Org. Biomol. Chem. 2005, 3, 48. https://doi.org/10.1039/b409018g
  26. Kim, S. K.; Singh, N. J.; Kim, S. J.; Swamy, K. M. K.; Kim, S. H.; Lee, K. H.; Kim, K. S.; Yoon, J. Tetrahedron 2005, 61, 4545. https://doi.org/10.1016/j.tet.2005.03.009
  27. Gunnlaugsson, T.; Davis, A. P.; Hussey, G. M.; Tierney, J.; Glynn, M. Org. Biomol. Chem. 2004, 2, 1856. https://doi.org/10.1039/b404706k
  28. Dryfe, R. A. W.; Hill, S. S.; Davis, A. P.; Joos, J.-B.; Roberts, E. P. L. Org. Biomol. Chem. 2004, 2, 2716. https://doi.org/10.1039/b408118h
  29. Benito, J. M.; Gomez-Garcia, M.; Blanco, J. L. J.; Mellet, C. O.; Fernández, J. M. G. J. Org. Chem. 2001, 66, 1366. https://doi.org/10.1021/jo001508n
  30. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647. https://doi.org/10.1016/S0040-4020(96)01094-0
  31. Fan, E.; Van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369. https://doi.org/10.1021/ja00054a066
  32. Yoon, J.; Kim, S. K.; Singh, N. J.; Kim, K. S. Chem. Soc. Rev. 2006, 35, 355. https://doi.org/10.1039/b513733k
  33. Wichmann, K.; Antonioli, B.; Sohnel, T.; Wenzel, M.; Gloe, K.; Price, J. R.; Lindoy, L. F.; Blake, A. J.; Schroder, M. Coordination Chem. Rev. 2006, 250, 2987. https://doi.org/10.1016/j.ccr.2006.07.010
  34. Amendola, V.; Boiocchi, M.; Fabbarizzi, L.; Palchetti, A. Chem. Eur. J. 2005, 11, 120. https://doi.org/10.1002/chem.200400592
  35. Breccia, P.; Van Gool, M.; Perez-Fernanedz, R.; Martin- Santamaria, S.; Gago, F.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 2003, 125, 8270. https://doi.org/10.1021/ja026860s
  36. Metzer, A.; Gloe, K. Stephan, H.; Schmidtchen, F. P. J. Org. Chem. 1996, 61, 2051. https://doi.org/10.1021/jo951436d
  37. Wong, M. S.; Xia, P. F.; Zhang, X. L.; Lo, P. K.; Cheng, Y.-K.; Yeung, K.-T.; Guo, X.; Shuang, S. M. J. Org. Chem. 2005, 70, 2816. https://doi.org/10.1021/jo048545p
  38. Wright, A. T.; Anslyn, E. V. Org. Lett. 2004, 6, 1341. https://doi.org/10.1021/ol036441f
  39. Lee, S. K.; Kim, H.; Jang, S.; Kang, J. Tetrahedron Lett. 2011, 52, 1977. https://doi.org/10.1016/j.tetlet.2011.02.067
  40. Sun, X. H.; Li, W.; Xia, P. F.; Luo, H.-B.; Wei, Y.; Wong, M. S.; Cheng, Y.-K.; Shuang, S. J. Org. Chem. 2006, 72, 2419.
  41. Fang, L.; Chan, W. H.; He, Y. B.; Kwong, D. W. J.; Lee, A. W. M. J. Org. Chem. 2005, 70, 7640. https://doi.org/10.1021/jo050913h
  42. Sessler, J. L.; Gale, P. A.; Cho, W.-S. Anion Receptor Chemistry; Stoddart, J. F., Ed.; RSC Publishing: Cambridge, 2006.
  43. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191. https://doi.org/10.1016/S0010-8545(02)00258-8
  44. Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419. https://doi.org/10.1021/cr010421e
  45. Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841 and references therein.
  46. Gunnlaugsson, T.; Davis, A. P.; O'Brien, J. E.; Glynn, M. Org. Lett. 2002, 4, 2449-2452 and references cited therein. https://doi.org/10.1021/ol026004l
  47. Voet, D.; Voet, J. G. Biochemistry, 2nd ed.; Wiley: New York, 1995.
  48. Kral, V.; Andrievsky, A.; Sessler, J. L. J. Am. Chem. Soc. 1995, 117, 2953. https://doi.org/10.1021/ja00115a041
  49. Kim, H.; Hong, J.-I.; Kim, H.-J.; Chin, J. Angew. Chem. Int. Ed. 2008, 47, 8657. https://doi.org/10.1002/anie.200803116
  50. Kim, H.-J.; Sakamoto, S.; Yamaguchi, K.; Hong, J.-I. Org. Lett. 2003, 5, 1051. https://doi.org/10.1021/ol034155y
  51. Sessler, J. L.; Mody, T. D.; Ford, D. A.; Lynch, V. Angew. Chem. Int. Ed. 1992, 31, 452. https://doi.org/10.1002/anie.199204521
  52. Job, P. Ann. Chim. 1928, 9, 113.
  53. Benesi, H.; Hildebrand, H. J. Am. Chem. Soc. 1949, 71, 2703. https://doi.org/10.1021/ja01176a030
  54. Hynes, M. J. J. Chem. Soc., Dalton Trans. 1993, 311.

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